An Offer of Services
by 332249
Summary: The Feds are always trying to catch the Winchesters (when they know they're alive, at least). When the Counter-Terrorist Unit finally catches Dean, Red takes an interest in meeting new people. Spoiler Warnings up to end of season 12!
1. Meet and Greet

"So, who is this guy, again?" Agent Ressler wondered out loud, watching the new prisoner in the plexi-glass cube usually reserved for Red. "And why does he rate the attention of the CounterTerrorism Unit? What did he do to deserve the Box?"

"His name is Dean Winchester." Special Agent Cooper answered. "He's been on the FBI Most Wanted list twice. Faked his own death three times. Each time he and his brother reappears, they up their game and the body count."

"Damn. I remember that name." Ressler swore. "Didn't they go on a killing spree a few years ago? Opened fired on a bank they didn't even bother to rob and then slaughtered a diner full of people?"

"That's them." Cooper agreed. "Dean Winchester there got picked up last night robbing a museum. He provided the distraction while his brother, Sam, got away with some kind of artifact."

"What artifact?" Ressler asked.

"Some ancient tablet or other." Cooper dismissed the theft. "The FBI is more interested in how Dean Winchester managed to leave behind two bodies with his exact fingerprints and dental records. He's _here_ because Red heard about the arrest and wanted to talk to the man and was willing to trade a free consultation on the case of our choice in exchange for an hour with the man. Agent Keen is bringing him in now."

Suddenly, the man in the box apparently decided he was bored. He began to belt out "Ride the Lightning" by Metallica at the top of his lungs, complete with air drumming.

"Red wants to talk to this guy?" Ressler repeated, surprised. "Why?"

"We will find out soon. He never said he wanted privacy." Cooper nodded at the door were Red had just walked in, Agent Keen with him.

Raymond Reddington walked past all the FBI agents and the guns. His entire attention was focused on the prisoner. "Dean Winchester," he greeted. "I never really expected to meet you in person."

The prisoner cocked his head, studying the older man. "I know you?"

Red chuckled. "No, we have never met. But I now of you, and your family business. I have even read your books."

For some reason the agents couldn't fathom, Winchester groaned and threw his head back and hands in the air. "Great. A groupie. Please, God, tell me you are not here to get my autograph."

"Actually, I almost wouldn't mind." Red laughed.

"Books?" Ressler whispered. "What books are they talking about?"

Cooper shushed him.

"If you actually knew anything about us, then you would know how much we hate those damned books." Winchester pointed out.

"I do know. I also know its real. All of it." Red explained. "I also know that you saved my life, some years ago."

The agents all leaned forward, wanting to hear the details even as Dean asked, "How's that?"

"You see, I was rather stuck in Chicago when the Pale Horseman came calling." Red told them all. "By the time I realized that he was about to wipe the city off the map, the storm was already picking up; grounding all flights out. I was quite certain I was about to die. And then, because of you, I didn't."

Winchester considered the man in front of him. "Okay," he replied, accepting the story.

The FBI agents were all surprised. Both men accepted as fact that one had saved the life of the other. But everyone could tell that, even though Winchester agreed it had happened, he clearly didn't expect anything from Red for his efforts and wasn't sure why the older man was bringing up the past.

"Pale Horseman?" Ressler whispered to Cooper. "I don't remember a hearing about an averted terrorist attack on Chicago."

"Neither do I." Cooper agreed, low-voiced.

"And while you stopped the leveling of Chicago, your brother stopped the release of a biological weapon called the Croatoan virus, I believe." Red sighed. "An associate of mine had hoped to keep a sample but your brother was very thorough. Probably for the best, considering."

"I also know that the assassins hired to eliminate Dick Roman were never heard from again. Even though they hit their marks. Especially because they hit their marks." Red continued. "But you and yours stopped him before he could decimate the American population by poisoning our food supply, in the…corn syrup, I believe."

"Asshole killed my foster father." Winchester told him, still studying the older man, trying to get a handle on him.

"Poisoned food supply?!" Ressler hissed.

Again, Cooper shushed him.

"And the corn syrup was phase one to make us stupid. Phase two was the diet food to wipe out all the healthy people." Winchester added.

"I am not a Hunter." Red offered. "No, I am a bit more like your Bella Talbot. I am aware of what you do. And I have run into a few monsters, or rather run away from them, over the years. Only I have no interest in exploiting the options they present. There are some lows that even I will not stoop to. Not many, mind you, but there are some."

"You're not a Fed, either." Winchester said. "Who are you?"

"Ah, of course, I neglected introductions. How rude of me. I am Raymond Reddington, somewhat colorfully known as the 'Concierge of Crime.' For a cost, I connect goods and services to various less-than-legal persons in need."

"So, what, you're craig's list for criminals?" Winchester asked, face twisted with derision. "Do you have a web site where I can rate and review? Assassin X gets three stars out of five, he killed the target the way I told him to, but he took forever. Assassin Y only gets one, moron killed the wrong target."

Red laughed out loud, choosing to take the prisoner's derision for humor. "That's a good idea. Maybe I should update. Then again, as I am now a criminal informant for the FBI, I am slowly turning in my client list. My own reviews would be the worst."

"Not that this chat hasn't broken up a very boring incarceration, but what do you want, Reddington?" Winchester demanded.

Red smiled. "I wanted to thank you. For saving my life, however inadvertently. And to express my deep appreciation and respect for the work you and your brother do. It has saved the lives of the very few people I care about in this world." He stopped there and held the younger man's attention. Silently communicating the depth and sincerity of his respect and appreciation until belief flickered in Winchester's eyes.

"I also wanted to offer you whatever services I can provide. The next time you need an ancient Sumerian tablet extracted from a high-security museum, or the next time you need enough ordinance to demolish a building, call me. If it is in the name of the work you do, I will assist however I can."

"At what price?" Winchester asked, tiredly jaded. "Offers like that always come with a price. And the I always get the short end of that deal."

"Aren't you a little young to have lost faith in human kindness?" Red chided.

Winchester snorted. Expressively. "That's not why you're here. You sound like a crossroads demon trying to ease a mark into a sell. And I haven't been that young in a long time."

"It's an honest offer." Red didn't seem offended by the demonic comparison. "And some day, when you're desperate, please consider calling me before Crowley."

Winchester flickered his gaze to his audience of federal agents recording every word. Lips tight and jaw muscles twitching, he asked, "You do prison breaks?"

Agents' jaws fell open at the man's audacity.

Red laughed. "If your brother and your friends don't manage something soon, I will see what I can do." Elizabeth Keen opened her mouth to protest. Red held up a hand to forestall her. "Starting with hiring you the best lawyer I know and calling a few friends in the state department that owe me some favors."

"The first one's always free. That's how you hook 'em in." Winchester predicted darkly. "Pass."

Red shrugged and made to turn away, but hesitated. Turning back, he asked one more question. "What's it like? The Basement?"

"Save the guy who saves the world. What? Hoping to Get out of Hell Free card?" Winchester snarked. Then he evidently saw something in Red's face that made him sober, an echo of his own expression before his deal came due. "Have you ever screamed so long and hard that the inside of your throat bled and you didn't want to stop screaming long enough to drag more air into your lungs so you could keep screaming?"

Red tensed and went just a shade paler. "Actually, I have," he answered thickly lost in the memory of the experience.

Lizzy snapped her attention to his face, more concerned than she'd like to admit.

"Now imagine you can't bleed out and you don't need to breath to scream and not even dying will end it." Winchester ordered. "That's what the Basement is like."

Struck mute, Red jerked a nod at the prisoner and walked away. Only to be accosted by Ressler and Cooper."

"Are you honestly trying to tell me that that psychopath," Cooper pointed at the Box, "saved Chicago and the country? That he's a good guy?"

Red smiled. "And saved thousands of other people, one or two at a time. Innocent people." He agreed. "But for some reason, no one ever believes them when they try to say so. All anyone believes is the body doubles used to frame them for mass murder. And yes, agents, they were very thoroughly framed by carefully designed body doubles. That man and his brother are honest to God heroes, and have paid every price it cost. So, if you will excuse me ladies and gentlemen, I am going to hire him a lawyer."

But even as the word "lawyer" passed his lips, all the lights in the building flickered off. For a few fast seconds, everyone floundered in the pitch black until electricity was restored. But in those few seconds, Red heard the soft sound of feathers rasping through the air. A smile spread across his face as he turned to look at the empty Box.

"You're welcome, Castiel." He murmured. "I'm glad you heard my prayers. Don't forget to give the boys my phone number, and tell them, 'Good Hunting' for me."


	2. A Paying Job

Dean's phone rang.

It wasn't an uncommon occurrence. Plenty of people had his phone number: Jodi Mills and her wayward girls, Garth and other Hunters, random truck stop waitresses and secretaries. Even a few non-humans had the number, like Cas and Crowley. On a normal day, he would answer it right away. As a Hunter, one never knew when someone in crisis might have just enough time, just enough breath, just enough battery, or just enough reception to call out for help. If a Hunter doesn't answer the phone, someone needing help might not get it in time.

Today, Dean really did not want to answer the phone.

His hands were covered in grease and engine oil. Dean was laying on his back under the Impala, depressed and more than a little upset. And in no real mood to answer the call for another job solving someone else's problems. The Impala, his Baby, his _**home**_ , was broken. Dead. Surrounded by parts and engine pieces, laid out on tarps like organs on a coroner's autopsy table, Dean had finally found the problem.

For all the good it did him.

The problem was that the vehicle was almost fifty years old and still in active use instead of resting comfortably in a climate controlled garage. The problem was that Chevrolet had discontinued parts for this make and model decades ago. The problem was that the late Bobby Singer's scrap yard had been long since gutted of all usable components because of all the previous rebuilds. The problem was that as good of a mechanic as Dean Winchester was (and he was damn good), some things couldn't be repaired; only replaced. And there were no replacements.

Resolutely, Dean decided that a job (or more specifically a chance to kill something) would only improve his mood. He also reminded himself that this was his duty to the Hunting community and the world.

Dean shoved aside his bleak mood and jabbed the speaker phone button with his cleanest finger without getting up. "Talk to me."

"Mr. Winchester," an unfamiliar voice greeted him. "I hope you'll forgive me for calling on you when you never gave me your contact information. But I have a line on a job that would require your and your brother's singular talents."

"Who is this?" Dean demanded. "How did you get this number?"

"Ah, of course. I am always falling behind with pleasantries when we speak. My name is Reddington; we met while you were in FBI custody and I made you an offer of services. I hope Castiel relayed my phone number to you?"

"Red," Dean recalled, his voice falling flat. "Crime Craig's List." It had been almost a year since they had met. Wasn't nearly long enough, in his opinion, between instances where he had to deal with the man's sliminess. "Wait, I thought you were supposed to be waiting for our call, not the other way around. Me and Sam are not butt-monkeys, we are not your clients, we don't got a profile for you and yours to rate and review." This last was almost growled.

"This woman has a supernatural problem. That is your area of expertise, is it not?" Red asked reasonably, ignoring the growling.

"Well, yeah..."

"Do you object to being paid for services you would normally volunteer?" Red asked, still in that reasonable tone.

"Paid?" Dean blinked as if the idea was a foreign concept.

"Yes, Mr. Winchester," Red chuckled lightly. "How about this: I will have a down payment delivered to the address of your choosing, which will be yours to keep no matter how things turn out. You will meet with the client to see what can be done. Hopefully, everyone can be satisfied."

Dean looked at his car again. "Not everything can be fixed," he reminded Red sadly.

"An unfortunate truth of this world," Red agreed. "But the down payment will still be yours regardless. If you can rectify the situation..."

"Yeah, yeah. I get rich and you get your cut. You do get your cut, right?"

"Naturally," Red acknowledged easily. "I always get something out of a transaction."

Dean rubbed his face tiredly. "You know what? Whatever. I'll talk in over with Sam. We'll let you know."

.o0o.

"How is she, Dembe?" Red asked through the phone.

"Confused. Scared." The big man rumbled. "Better."

"The Winchesters did it, then?" Red needed verification. "They cured Lizzy?"

"Yes," Dembe confirmed. "She is no longer a vampire. The cure was..." Dembe groaned over use of the next word coming out of his mouth, "...trippy...enough, that she believes everything that happened to her was an hallucination. I told her she had been drugged."

Red chuckled. "Did that term come from Dean? Did it hurt when you had to repeat it?"

"Yes," Dembe growled, answering both questions.

"She's fine, then." Red sighed in relief. "And ignorant of the supernatural."

"She is fine, brother." Dembe reassured the older man. "The Winchesters said we were lucky I had blood from the vampire that turned her still on my knife. I will see her home tomorrow."

Red ended the call.

.o0o.

"Wonder who she was?" Sam mused as the brothers sat in a 'borrowed' car, puttering down the highway. "Red's client."

"Dunno," Dean rubbed the red mark on the left of his jaw. "I'm going with bodyguard-assassin. Chick had a mean right hook. And she was with him when those feds had me in that box."

Dean's phone rang, playing 'Dangerous' by Royale Deluxe; downloaded just for Red so he would have some warning next time. Dean put the call on speakerphone. "The girl...she wasn't a client, was she? She's your family." He demanded without preamble.

"I have been asked before, and will keep answering: Lizzy is not my daughter." Red countered, unoffended at the brusqueness.

Dean snorted. "Don't mean she ain't family. I saw her worried about you, when I was in that box. Now you're pulling out all the stops for her. Family don't begin or end in blood. Like I said, she's part of your family. Her and that big guy. Blood's got nothing to do with it."

It was Red's turn to fall silent. "Its...dangerous for me to have connections like that."

Dean huffed a bitter laugh. "Its more dangerous to not. Connections like that keep us human."

Red changed the subject. "I found your down payment in a private collector's basement. There is also a bearer bond for $200,000 with it."

Sam almost choked. "That's a lot of money."

"You provided one of a kind services," Red pointed out. "Next time negotiate your fees beforehand. Until then, gentlemen."

Both brothers were lost in thought, trying to figure out what the down payment was. Until they pulled into Singer Salvage yard (the agreed on drop spot). That's when they saw it: a mint condition 1968 Chevy Impala, cherry red. When they looked closer, it had less than one hundred miles on her; practically factory pristine. Spare parts, still in the boxes, filled the trunk.

Dean looked to his brother in shock. "I can fix Baby."


	3. A Bad Idea

Hunters like to think of themselves as men of action, as bad-ass fighters who can get thrown through a wall as shake it off. Very few Hunters brag that they pulled a research marathon, going almost thirty hours without sleeping until their butt went numb before finding that little detail that saved the day. Research wasn't glamorous; it didn't help pick up a one night stand in a bar. But it was absolutely necessary. A good aim won't save a Hunter's life if he has the wrong kind of bullet hitting the heart instead of the head.

Sam and Dean Winchester knew this truth. Yes, they had the grit and the nerve to stare down any monster they came across. They also had Bobby Singer's lore collection, the journals of the Campbell family through the generations, and the Men of Letters library. They knew they had to figure this out before it was too late.

They were coming up short.

Cas was dying.

Stien family survivors knew how to do their research, too. They knew the Winchesters were vulnerable when desperate, and became desperate when one of their own lay on the chopping block. The Stiens also understood strategy; surprise only comes once so one must strike at the most powerful first and in doing so break the spirit of those left standing.

Rowena had proven that even angels were susceptible to curses.

For over thirty hours, the brothers has worked to find a way to save their friend; to locate and translate a purification ritual to heal a wounded or cursed angel. But like all powerful workings, there was always that last ingredient or artifact that was going to cost or was hard to find. In this case, it was bronze from the serpent Moses used to heal the Israelites.

"Its not here anymore," Sam announced not looking up from his file. "Says here that it was returned to Father Lilliman for transport back to Vatican City in 1952. Turns out back in the day, the Catholic Church shipped out a lot of the relics in the Vatican's vaults to allies during WWII to keep them safe from the fighting. Everything eventually got sent back, but in the meantime the Men of Letters got to play with the Church's toys."

"Awesome for them," Dean drawled. "Does it say that the Men of Letters have a library card to the Vatican? Can we borrow it back?"

Sam flipped through a few pages in another file. "Uh... there used to be, actually. But I bet all this contact information if defunct. And then we'd need written approval from a local bishop to go with the request."

"So we convince a bishop to help us out and have him set up the meet and greet with the Pope or whatever. We are trying to help an angel. That's doable, right?" Dean looked at his brother hopefully.

Sam sighed. "If, and that's a big if, if we find someone in Vatican City that remembers the Men of Letters we'd still have to prove that we are them. I mean, we're Legacies, sure. But guys like Henry aren't going to just hand this priceless, irreplaceable, _powerful_ artifact over to a pair of jumped up Hunters with a history of nearly ending the world on accident."

"Okay, then we don't ask." Dean wouldn't give up, not with his best friend on the line. "We fly to Rome and we steal the thing." It was a measure of Dean's concern that he volunteered to fly.

"Dude, this isn't some small time auction house or county historical society exhibit!" Sam objected. "It's the freakin' Vatican! Out of our league doesn't begin to describe the security there. It has its own police force of well-trained religious fanatics."

"Okay, so we convince another angel to come with us and do a glowy angelic declaration that they should hand it over," Dean tried again.

"Heaven hates us," Sam reminded his brother. "And most of Heaven hasn't forgiven Cas for the whole Lucifer out of the cage thing. They're not gonna help."

"It saved their asses," Dean grumbled, but without any real heat. No one knew better than the Winchesters how it felt to be on the outs with everyone for doing what they thought was right, screwing up royally, and then fixing it. "Okay, if heaven won't help, we try hell. Crowley has a cover ID as a catholic priest. We get him to pull the right strings."

Sam just looked pained, he hated the King of Hell and hated even more that his brother was so comfortable with the demon. "Then we owe him one."

Dean winced at the thought. He never forgot what Crowley was, and he knew that the demon would cash in that chip at the worst possible moment in the most painful way possible. "He probable couldn't do it anyway. His position Downstairs is a little weak right now; the demons almost wouldn't follow him to stop Amara in that last throw-down. Helping us again would eat at his credit."

Then a voice filtered through Dean's head, an echo of a memory: " _I also wanted to offer you whatever services I can provide. The next time you need an ancient Sumerian tablet extracted... If its in the name of the work you do, I will assist however I can... And some day, when you're desperate, please consider calling me before Crowley..."_

"Sammy, I've got an idea. But we're not gonna like it."


	4. Services Rendered

Elizabeth Keen stood on a balcony enjoying the view of the sunset. It really didn't surprise her that Red's idea of a safe house was a villa overlooking one of California's bigger vineyards. She was only surprised that it wasn't in Italy. Red himself lounged not far behind her, sipping at his tumbler of cognac and also enjoying the view. He'd been showing her his world, that bizarre mix of the finest things in life and its brutal, bloody underbelly.

She'd had her eyes opened and still couldn't believe what she'd come to. Although she had come to understand the careful dance of threats and bribes and Dembe's vigilance that Red used to buy these rare moments of peace and contentment. He was a master at that dance, having perfected the steps with a lifetime of practice.

Her little slice of peace was interrupted by someone's cellphone playing "Little Lion Man" by Mumford and Sons. Lizzy turned to stare at her companion, surprised at his choice of ring-tone. The music style really didn't seem to suit him.

 _Weep, little lion man, you're not as brave as you were at the start..._

"Red?" she asked tentatively, not sure if she should ask. "Who is it?"

 _It was not your fault but mine. And it was your heart on the line. I really fucked it up this time. Didn't I, my dear?_

Red considered his phone with a face showing his pleased surprise. He'd downloaded that song specifically for one man. Someone Red wasn't sure would ever call. He pushed the green button. "Well, hello." He listened for a moment, before his eyebrows shot up in even more surprise. "My, my. Knocking over the Vatican. Goodness me. Of course, I knew that if you ever came calling you wouldn't ask for anything small."

Lizzy felt her own eyebrows climb on her forehead. Knock over the Vatican? Really? She wasn't overly religious, and her association with Red had done much to make her reconsider her definitions of right and wrong, but the idea still left a bad taste in her mouth and a hard lump in her stomach.

Red had paused, listening to the voice on the other end of the line, and his face settled into something a little sad. "I am sorry to hear that. Truly."

To Lizzy's ear, he actually did sound sorry.

Red paused again, then chuckled. "Before Crowley, yes, thank you for that. I believe I know how to get that done." Another pause. "For you and your brother, free of charge."

Lizzy blinked in surprise. Red never did anything for free, if he didn't want money for services up front then there was an angle we was playing. She wondered if the person on the other end of the line knew that.

"Would it make you feel better if I charged you something?" Red asked of the caller.

Apparently, the voice on the other end did know Red, at least a little bit. Enough to know to look a gift horse firmly in the mouth when dealing with the man.

"As I said before, you two already have credit in my store. I will make the arrangements. Would you like delivery to the salvage yard as before? Very well. As soon as possible, yes." Red hung up the phone, a small smile spreading across his face.

"So, what's the catch?" Lizzy asked.

"Hmm?" Red shook himself out of his musings to look at her.

"They're right, you don't do anything for free." Red opened his mouth, but Lizzy continued. "Or at least, you don't do anything without strings attached or without an end game. And you just agreed to hire someone out to rob the Vatican. So, I repeat, what's the catch?"

"Ah, Lizzy." Red sipped his cognac again. "The catch. That was Dean Winchester on the phone. I imagine you'll remember the man who disappeared without a trace from the CTU's Box."

"Yeah. The guy you said saved Chicago and the FBI think is a serial killer." She did remember. "No one ever explained how he escaped."

Red laughed, a sound full of honest merriment. "No, I don't imagine they did or they ever will."

"But you know...?" Lizzy prompted.

"Dean Winchester and his brother are the men who mixed the anti-toxin for you when you had been poisoned. Though Dembe tells me you don't remember them being there."

Lizzy gaped. She had a few vague memories of those couple of days, of being desperately thirsty. Dembe had held her back while another man she couldn't put facial details to poured the most vile thing she had ever tasted down her throat.

"So yes, my dear. I will help them. If for no other reason, than they have very specialized skills and knowledge that might one day save my life, or yours again. Now." Red put down his drink and hauled himself up. "Enough background. We have work to do. There are only so many men with the capability of successfully penetrating the Vatican vaults..."

.o0o.

Two days later, Red's phone again played Mumford and Sons as its ring-tone, but this time was a new song: "Broken Crown."

 _Crawl on my belly til the sun goes down, I'll never wear your broken crown. I took the rope and I fucked it all away..."_

"Hello, Sam." Red answered. "To be honest, I expected you to leave the dirty work of dealing with me to Dean. He's alright, I trust."

"Yeah, he'll be fine; just got a little beat up catching one of the ingredients," Sam confirmed.

"And Castiel?"

"He'll be fine, too. So, you know, thanks. For helping us out."

"You are most welcome." Red hung up the phone.

Dembe moved to stand next to him. "Are you sure they are worth it? Can they help you? Will they?"

Red hummed. "If properly motivated, they can."

"They can be dangerous men, brother. If they realize you have been cultivating them for your purposes." Dembe declared, warning and concern warring in his voice.

A broad smile slid across Red's mouth. "Dangerous? True. But don't worry, Dembe. I am being very, very careful with the Winchesters."


	5. A Concerned Conversation

A/N: If you haven't read the other SPN/BL crossover "Mister Crowley" by VivaRex, I highly recommend it for its own sake. It's an excellent bit of writing. My story wasn't originally meant to go with hers, but I found myself taking her fic as part of my head-cannon's back story. I hint at it in this piece of my story, but if you haven't read it, it won't interrupt anything. Thanks again to all my readers!

.o0o.

"Squirrel, to what do I owe the pleasure?" Crowley's voice purred over the phone line. "Is the world about to end again? Because, that whole routine is getting older and older every time, Darling."

"Raymond Reddington. You got a Deal with him, don't you?" Dean Winchester's voice seemed abrupt but not angry. This wasn't a social call, but a fact-finding mission.

Crowley paused over the phone, mind whirring out the possibilities and the scenarios. In a fraction of a moment he weighed out the pros and cons of half truths and well crafted lie. But then, this was Dean. Dean Winchester asking about Red, the two humans alive on this earth that knew him best. Interesting. "Yes, I do," he answered finally.

"Wow. A straight answer. Are you okay? Did it hurt?" Dean asked with mock concern lacing his voice.

"Get bent," Crowley suggested mildly. "Why the sudden concern about Red? Has he done something naughty? Should I be jealous?"

Dean snorted loudly into the phone.

With a long-suffering sigh of disgust, Crowley pulled his phone away and made a show of cleaning his ear of imaginary spit and snot. Not that anyone could see him doing it, but it was the principle of the thing.

"When's his Deal come due?" Dean demanded

"Hmm..." Crowley scratched his beard, considering again. Finally, he went with a little bit if truth again, curiosity getting the better of him. "Open ended, actually. Thinking about saving him from himself?"

"Open-ended? How's that work?" Dean blinked in surprise. Deals were standard issue: ten years. His dad's, his own, and Becky's to mess with Sam were the only ones he'd ever heard of that were special cases.

"Raymond Reddington has a unique skill set and contact list that I find useful from time to time." Crowley poured himself a glass of fine brandy and settled into his chair. He knew this conversation would take a lot of energy. "When he dies, I get his soul, but I never put a time limit on the contract. I do appreciate getting full value out of my investments."

Silence from the other end of the line meant that it was Dean's turn to consider, to run the scenarios. Crowley waited patiently. He knew, like Sam knew, that the elder Winchester was not as dumb as he let the world believe. Oh, he was lacking in knowledge base, obviously. And he had no patience for politics whether of human or demonic or angelic variety. But the Hunter knew strategy; he understood application of resources.

"He goes where demons can't. Gets things don't when you don't want demonic signs to tip your hand," Dean realized. "Clever."

"His proposition, actually," Crowley chuckled in amusement. "Didn't like the idea of dying young after a mere ten years, I daresay. What clued you in? Did he ask for help?"

It was Dean's turn to be amused. "Nah, not yet. We're still in the schmoozy, wining and dining stage. God, this guy, Crowley. Every time I talk to him I have to take a shower to get the imaginary slime off of me. I get the feeling this guy actually deserves his trip Downstairs."

"He makes you feel dirty?" Crowley teased, letting his voice go deeper and seductive. "And hear you've spent all this time playing coy about your preferences." Over the phone, the demon couldn't see the hunter roll his eyes but he knew that's what was happening. "Take it from me, Squirrel, he's a decent kisser."

"Gah!" Dean groaned. "I did not need that image in my brain, Boris. Well, at least you know he won't be squeamish when you put him to work making Deals of his own. A slimeball like that will make one hell of a crossroads demon."

"Part of Deal making is a recruitment drive," Crowley reminded. "Have to keep the ranks and file coming in full and all that drabble."

"How long do you think it'll take him to turn? Are we going to have to deal with Demon Red in our lifetimes? Because I am not looking forward to that. Guy that slippery? I bet he's been grooming that hot not-his-daughter to hold the fort for him while he's away. And he's got that big, black dude absolutely loyal to him. That's hard to find. I mean, come on. _You_ don't have loyal minions. He's gonna be a problem."

Crowley stilled in the middle of sipping his brandy as the words penetrated. Dean let the silence hold as the demon ran through the permutations. "Dean, you bastard, I know what you're doing."

"Doing?" Dean asked, all innocence.

"This is your version of trying to be sneaky, but you're not very good at it." Crowley shook his head in mock disappointment, knowing that Dean couldn't see him but also knowing the hunter would know he was doing it. "Not so subtle hints that _I_ would be better off if I let this one contract go. As though I couldn't handle Raymond Reddington, human or demon. I am the bloody King of Hell."

"You're the King of Hell," Dean agreed. "And no, I don't do sneaky or subtle. But you gotta admit, I got you thinking. I can hear hear the clockwork turning from here.

"So, what, Dean? Am I suddenly supposed to just rip up a valid contract and let him go skipping off to enjoy his lovely, new-found freedom?"

"Oh, hell no," Dean laughed at the very idea.

"Come again?" It wasn't often a Winchester truly surprised the demon. They were both predictable in their own little ways. The elder brother had a long-established and well-defined hero complex; he had to save people, most notably his little brother. But any old person would do in a pinch. Usually, anyway.

"I said 'hell no,' Crowley," Dean repeated. "I've seen the crap he's done; had Sam pull his file. Besides, he's still in the wine and dine phase. How much you think he's going to spend on us before he pops the question? Did you know he chased down a Chevy Impala compatible with mine so I could keep her running?"

Crowley huffed a laugh as understanding dawned in him. "He does his research, I'll give him that. And dare I believe my ears, Dean? You want to milk this cow as far as he goes."

"I do. I'm thinking it could take awhile." Dean eased himself back on his bed, Crowley could hear the mattress creak. After a moment, the human sighed and admitted, "I can't figure out what his end game is. I mean, even without a contract what are the odds that guy ends up anywhere but Down? Getting him off doesn't win him much. And if he doesn't want out of his deal, if he's planning of becoming a demon, why bother trying to play footsie with me? I mean, I'm kinda known for killing you black-eyed sons of bitches."

Several ideas ran through Crowley's head, some good for him and some extremely bad. "Well, we will have to wait and see. I'm ashamed to admit it, Squirrel, but I think I have been ignoring dear, old Red lately. Perhaps I should remedy that."


	6. Friendly Advice

Elizabeth Keen was often confused about Raymond Reddington, had been since the day they met. She was sure most of it was a conscious, conscientious effort on Red's part to keep things that way. But after everything that had happened with Fulcrum and with Tom... She really needed to sort out a few things concerning Red.

A sounding board was her usual way of working out problems. Getting things out in the open and said aloud made her organize her thoughts, forced her to put all the data and facts floating around her head into coherency.

But who? Red had his own agenda; that much had been obvious from day one (even if no one knew what the agenda _was_ , everyone knew one existed). Likewise, Tom had his own ideas about everything. The FBI had a party line and all the agents she knew with clearance to listen to her would stick to that party line. All of her more casual friends didn't have the kind of background to understand and she had no real desire to explain it to them.

No, what Lizzy really needed was someone who already knew a little about Red. Someone who was neither a government agent or an established enemy, yet still had some kind of working knowledge of the man.

The song from her radio caught her attention: "Little Lion Man." That was the ringtone Red used for Dean Winchester. She had seen the phone number on his phone's screen back then and made the effort to remember it. Dean Winchester. The other man who had earned the box. One of the few men that Red said good things about.

She just hoped he'd be willing to meet her.

.o0o.

Elizabeth Keen sat in a coffee shop across from Dean Winchester, both with a mug of something warm sitting in front of them.

"I need some advice. From a new perspective," Lizzy opened the conversation.

Dean cocked his head, curious despite himself. "So you ask the wanted serial spree killer? Sweetheart, you need to rethink your approach to life. Cuz, that's messed up."

"That's what the FBI files say about you and your brother, that you're psychotic murderers," Lizzy agreed. "Red says you're not. He says you're heroes. Said you saved my life when you cooked up the antidote when I was poisoned."

Dean grimaced. "Well, this is awkward."

"What?"

"You want to trust me because of Red's recommendation." Dean's face showed his surprise.

"That's a problem?" Lizzy asked.

Dean didn't answer for a moment, thinking how to word what he wanted to explain. "Do you trust Red?" he asked instead of answering.

Lizzy recognized that this man wasn't avoiding the question, he was trying his best to answer an extremely tricky question. She sighed in annoyance, even so. "That's what I need advice about."

Dean groaned. "Awesome."

"Do you trust Red?" Lizzy threw the question back at him.

"Absolutely not," Dean returned without a moment of hesitation, without needing to think about it. "I trust Raymond Reddington about as far as _you_ could throw _me_."

"What?" Lizzy was surprised. "But... He calls you for help. And you called him for help, when you needed to rob the Vatican. Doesn't that imply some sort of mutual-?"

"No," Dean cut her off. "That implies desperation. A friend was dying, we got desperate. _That_ was the only reason I would ever go to Red."

Both man and woman fell silent for a moment.

Gently, Dean asked, "Why do you want to trust him? You got to know how shady this guy is."

"I _do_ know, its just..." Lizzy threw her hands up in frustration and began to pace. "He knew my mother, before I was born. When she died, Red made sure I was adopted by a good man. When I got older and moved out on my own, he hired a guy to watch out for me, a kind of bodyguard."

"Okay, that would make an impression," Dean admitted, running a hand over his face tiredly.

"Why do you work with him if you don't trust him?" Lizzy asked.

Dean contemplated his drink, then studied the woman in front of him. "In my line of work, Red is a little fish. I have seen evil on such a massive scale... he doesn't hold a candle to it, not in the grand scheme of things."

Lizzy blinked. Red? A little fish? But he always seemed so... larger than life to her.

"I know he's got an endgame. Guys like him always have an endgame." Dean sipped at his coffee, trying to form thoughts into words. "I can work with him, because I know he's not gonna knife me in the back until I'm not useful anymore. Until he gets everything he can from me or when I start actively opposing his plans. When that happens- _when_ that happens, not if, _when-_ all bets are off. I become disposable. No matter how helpful he will be to get on my good side, I cannot and will not forget that: I can easily become disposable."

"You think he's just using me," Lizzy whispered. If she was being honest with herself, it shouldn't surprise her. Still, it hurt. Just a little.

Dean blew out a frustrated breath. "I don't know. When you vam-" Dean cut himself off before he said 'vamped out,' remembering just in time that she wasn't told about the supernatural. "-when you were poisoned, and Red called us in... I could tell he cared about you. More than just as an asset."

"Really? How?" Lizzy demanded.

"Mostly the way he avoided talking about it," Dean admitted. "You had to read between the lines to see it."

"Oh."

"Sweetheart, you want my advice? Don't let your guard down because you think he might care about you or you care about him. Whether he likes you or not, he will always be dangerous to you. Guy like him? For the right price, or at a high enough cost, he will betray you. Even if he doesn't want to, even if he will grieve your loss later, he will always be capable of it. I've seen it happen."

Both parties lapsed into silence again, deep in thought. They both had to let this conversation sink in. To break up the awkwardness, they nursed their coffees.

"I-uh... I have something for you," Dean broke the quiet eventually. He set a small pendant and cord on the table.

Lizzy picked it up. There was some kind of stylized star stamped into the metal. "What's this?"

"I know one of the guys Red has to answer to, Crowley. Know him too damn well," Dean admitted. "Whatever he wants, Red has to do. This guy is a real piece of work and he wouldn't think twice about killing you, brutal and bloody. This," Dean tapped the pendant, "will make him think twice. I know you got no real reason to trust me, but it'd be a real good idea if you put that on and never took it off."

"Red answers to someone?!" Lizzy demanded. The questions lined up on her tongue so fast, she wasn't sure she could spit them all out. "Who? Why? How?"

Dean held up his hands. "Its not like that. Red does his own thing ninety percent of the time. But when this guy snaps his fingers, Red has to jump. That's the price of a deal they made between them years ago."

"What did Red get out of it?"

Dean shrugged. "Don't know, didn't ask."

Lizzy settled the pendant around her neck. "You know, I asked you to meet me to get answers. Now I just have more questions."

Dean finished the last dregs of his coffee. "You're hanging out with Red. There will always be more questions than answers. Trust him if you want, but always have a plan B ready."


	7. The Plan

Dean stared at his wall covered in papers. Just stared. It was crazy. _He_ was crazy. But... sometimes crazy worked. Sometimes crazy was the only game in town.

The idea for this craziness had come to him as he rebuilt his Baby. Raymond Reddington has been on his mind because Red had gotten the parts Dean was using, payment for services rendered. With thoughts of Red came thoughts of Demon Deals and Crowley and Hell. And what to do about Red. The guy was not a man Dean wanted to be three steps behind.

Dean began to wonder if it was even possible, his crazy little idea.

That idea was so out there, Dean never said the thought aloud. Merely let it percolate through his brain. Besides, saying something out loud meant the possibility of being overheard. Crowley had bugged the Impala before with that little gold coin, the son of a witch. Bugging the Impala again with more mundane means was not beyond Reddington. Somewhere in the back on his mind, he heard Frank Deveroux laughing about who was being paranoid now, but he ignored the voice. Even so, he didn't say it; he wrote it down instead.

Dean wrote the bits and pieces of the idea and the items it would take to make it happen on bar napkins, motel stationary, and on the back of diner receipts as inspiration struck. Then he stuffed the bits of paper in a pocket, wordless still. Then he brought them back to the Bunker to throw them all in the same wire wastebasket. Sam never really noticed that there was one trash can on Dean's room that never got emptied (it wasn't like it was ever Sam's job to clean Dean's room.)

Scraps of paper of ideas collected until one day when Dean sat down at his desk (yes, he had a study desk in his room) and lay them all out in a row. Piece by piece, Dean taped scraps of paper to the wall in order, adding more notes and details as he went, until there it was: the Plan, all laid out and doable. In theory, anyway.

As Dean had scribbled ideas, he had also doodled bits of map and directions on the back of completed hunt research printouts and in the margins of newspapers. Crumpled balls of paper joined the scraps in the wire wastebasket. As the plan was assembled, so too were the maps.

Dean tacked two blank poster boards on a different wall. All around them, he taped the doodles and sketches and directions. Painstakingly, he began to draw in earnest, recreating each drawing and doodle on the poster board in scale with each other. Until he had two complete maps drawn from memory on the wall. And a path clearly marked as a dotted line in pencil running through them.

One of the maps had been hard to draw. Some memories caused no end of nightmares. But the crazy idea would not leave him alone. So he pushed through the bad night's sleep. Now here it was.

It was time to embrace the crazy and run the whole plan past Sam and Cas.

.o0o.

Sam and Cas had followed Dean to his room when he asked. For several minutes, both man and angel stared at the wall. John Winchester taught his boys how to map out a hunt on the wall. Sometimes it took this step back and enforced organization to understand what they were looking at. Sam saw the same style on that wall. However, being organized did not mean he wasn't nuts.

"Is that a map of hell?" Sam demanded. "Where did we get a map of hell?"

Dean shrugged. "I drew it from memory. Cas, man, feel free to point out anything you recognize that I got wrong." At Sam's look, Dean felt compelled to explain. "Alastair, after I broke, used to take me with him to tour the dungeons to find subjects to work on. He never left me unguarded, but I saw a lot of the place over a decade."

Once he read the whole wall and understood, Sam exclaimed, "Dean, this is insane!"

"Follow the logic, Sam. Tell me what's not possible." Dean was not deterred by his brother's initial resistance. "Go to Wyoming. Fix the Devils Trap train tracks where it broke. Go to the cemetery. Lay down another set of demon warding, the strongest the Men of Letters knew how to make." Dean pointed to a photocopied ritual on the wall. "We've got all the ingredients. Use the Colt to open the Devils Gate. Between the railway and the warding, nothing will get out." Dean traced a finger along the dotted line on the map. "The other side of the Gate comes out around here."

"In Hell!" Sam yelled. "You're talking about waltzing into hell!"

"It took a garrison of angels to rescue you, and there were losses, Dean." Cas reminded, voice remorseful. "The three of us would not be enough."

"We wouldn't be _invading_ hell, guys. We'd be sneaking in the back door." Dean retorted. "The Gate opens in an old, deep part of Hell. Not too far from the cage, actually. It's mostly empty over there; all the big bads already got loose."

"Your living, human souls would draw attention to us, Dean. Much like you did in Purgatory." Cas objected. "There may not be much, but everything in the vicinity would come like a moth to a flame."

"Yeah, I thought of that, Cas." Dean gestured to another photocopy of sigils. "Look familiar?"

Cas squinted at the paper. "Its similar to the tattoos I had put on myself for concealment."

"Similar," Dean agreed. "But when me and Sammy draw these on using that potion," He pointed to a recipe taped to the wall. "It'll work like a camouflage net. Witches will think we're witches, angels will think we're angels, and demons..." Dean trailed off.

"...will think we're are fellow demons. Probably in our forms in order to torment someone, like they did to Bobby." Sam finished in amazement.

"Yatzee." Dean grinned before taking up his narration again. "Cas stays behind to make sure the Gate closes. Me and Sammy sneak around here, where every single demon deal ever made is stored, and we torch the whole place. Everything. No contracts means nobody gets collected and dragged Downstairs by hellhounds. At least, not until demons can go around and get everybody to re-up their Deals. Assuming that those people haven't had a change of heart since they first kissed on it. Think about it, Sam: no deals come due for ten years. Think about how much that will weaken hell and piss off Crowley."

"Dean, contracts don't just burn..." Cas began.

Dean pointed at yet another sheet of directions.

"Blessed fire," Sam read. "We found that ritual back before your Deal came due, in case we ever caught up with whatever demon held your contract."

"I can make firebombs and flamethrower fuel out of the stuff." Dean explained. "Enough to demolish the Library of Congress if I wanted."

"That... that would be sufficient," Cas nodded slowly.

"Then, as everyone goes nuts because of the fire, me and Sammy make a break for it back to the Gate. Where we get on the soul phone and ask Cas to open the door back up for us. Easy as pie." Dean let his hand drop. "Question?"

"Why the map of Purgatory?" Sam demanded.

"Plan B." Dean returned promptly. "If something happens to cut us off from that exit, we take the long way around." He pointed to another dotted line. "Past the holding cells were they kept Bobby, through Purgatory, back to earth in Maine."

"Wow. A back-up plan." Sam laughed.

"I know. Concept, right?" Dean chuckled. "I didn't want to half-ass this."

"Why now? What brought this on?" Sam asked.

Dean fell silent for a moment to find his wording. "Raymond Reddington. I don't want Crowley to have a contract over him anymore." He took a deep breath, knowing they might not like the next part. "I don't want to burn it just yet, either. I want it in our hands. At least until we know what in the hell he's up to, I want leverage on him. 'Cuz the guy is dangerous and up to something. I don't like not knowing what."


	8. Contracts and Obligations

Crowley was upset. No, he was beyond upset. Beyond mere anger, beyond incensed, beyond livid. None of the many, many languages he knew contained a term powerful enough to convey the sheer magnitude of Crowley's rage over what had been done to him. This was the seat of his power, soul contracts; gone up in holy smoke.

All over the world, crossroads demons were scrambling in all directions, looking up old customers and offering a 'ten year extension' if they wanted their deal back. Many were happy (or some approximation of the emotion) to have their power, money, fame, talent or whatever it was that they had bargained away their soul for originally restored. By Crowley's count, too many changed their mind. A lot of people too close to their original due date and feeling their own mortality were no longer desperate enough to deal again.

Losses were running about 50/50. It was a blow, no doubt about it. And while his crossroads demons (plus a few more borrowed from other departments) went forth to woo back old clients, there was no time to pursue new contracts. It would take the King of Hell several _years_ to recuperate losses and build back up to full capacity. As a cherry on top of this nasty surprise of a sundae, no contracts meant a forthcoming labor shortage in his future.

Fuming, Crowley resolved to design an entirely new form of torture for whoever did this. He had a short list and a longer list of anyone and everyone capable of doing this. If he couldn't figure out who was actually responsible, Crowley planned on killing them ALL. Slowly.

In the meantime, Crowley did not exempt himself from the task of revisiting old clients. There were quite a few; he was good at his job. But the former King of the Crossroads remembered every man and woman he dealt with and what they dealt for. (Unlike some of his flunkies who might have to be terminated when he could afford the loss.) Securing old contracts severely undercut his available time to investigate the breech of the Contracts Vault. And its security upgrades.

One by one, Crowley checked off names from his list, starting with his most recent and working his way back. Last on his list, his longest standing contract? Raymond Reddington. Concentrating on his magic inherent to his corrupted nature, the demon verified what his senses told him: Raymond Reddington's contract was still intact.

Whoever had razed a little hell, had taken the time to remove at least one contract. Where there others missing in action but still alive? How in the eternal holy hell would Crowley tell what wasn't destroyed from the ashes?

Well, he knew where to start.

.o0o.

Raymond Reddington couldn't say he loved many things. He did enjoy a multitude of pleasures, however. Today he indulged himself in one of the simpler things in life: a perfectly fitting suit of clothes. Really, really skilled tailors were distressingly hard to find in the United States. That's why Yanof was such a find. The ex-patriot of Slovenia possessed an amazing eye for fabric lines preternaturally talented fingers. Sadly, his client base in this country was growing very slowly due his lack of facility with English. Happily, Red's grasp of Slovene was more than up to the task of expressing his needs.

"I see the next time something eats my tailor I should ask you for a replacement recommendation," a cool British voice mused from behind.

Yanof startled and cried, " _Tristo kosmaith medvedov_!"

Red muffled his own exclamation as Yanof accidentally jabbed one of the pins into Red's flesh in his surprise.

Crowly chuckled. "I love Slovene expressions. 'Three hundred hairy bears' instead of 'bloody hell.' Always makes me laugh."

Yanof's cry brought Dembe running into the room, gun drawn. Lazily, the demon waved a hand throwing Dembe in one direction and his gun another. The big body guard rolled back to his feet after impact and growled his displeasure, but made no further moves against their surprise visitor. He knew it wouldn't do much good; no matter how much he disliked Crowley.

Gingerly, Red removed the needle from his hip. "Ah, Mister Crowley, it has been forever. To what do I owe the pleasure?"

"Business, Darling. Not pleasure."

"If you can't mix a little bit of the latter into the former, then what's the point?" Red countered neatly. He handed the tailor the offending pin and shooed him off. If the King of Hell shows up unexpectedly, it wouldn't be for social obligations. Not to mention that a man needed all his faculties focused when dealing with the being. These interactions well and truly kept Red on his toes.

"True, I do enjoy my work," Crowley agreed. "How have your endeavors been going, Raymond? How is our precious little Lizzy these days?"

Red kept his body relaxed even though he hated, passionately, whenever the demon mentioned Elizabeth. "Things with the FBI are progressing more or less as expected. Excepting a road bump or two. But nothing so detrimental that the end goal is out of reach."

Crowley smiled. (Not that the expression did anything to ease Red's mind.) "Yes, all roads to victory. I've never known you to have only one rod in the fire. Quite the impressive juggling act you have going with them."

"One must be flexible," Red shrugged.

"One must also know when one is overreaching." The demon's face never lost its amiable expression. "No matter how well you manage, with your hands that busy something is bound to slip through your fingers. When was the last time you spoke to dear Elizabeth?"

Anger and worry flared up in Red's heart: the Kind of Hell did not go out of his way to mention a human woman twice without some kind of threat underneath his words. Even so, Red picked his response carefully. "It was my understanding that you are contractually obligated to keep Elizabeth healed of her original injuries as well as her safety from mental or bodily harm from demonic activity or possession. From all demons, yourself included."

"Ah yes. That little addendum," Crowley murmured, before turning to face Red square on. "It seems you have a problem."

Red's surprise showed clearly on hid face. "Have I not kept my obligations to you?"

Crowley nodded. "You have. Beautifully, I might add. But you see, you were never obligated to me, personally. The contract clearly stated that you are beholden to whoever holds your contract. I wasn't going to let a soul off the hook if something happened to my handsome self."

Mind cycling through possibilities, Red realized something. "You lost my contract." He couldn't keep the awe and hope from coloring his voice.

"I lost ALL the BLOODY CONTRACTS!" Crowley bellowed. Electricity flickered and several light bulbs shorted out. Sparks and shards of glass flew in all directions.

Dembe started a soft but fervent prayer in his own language in the face of such a uncontrolled display of power. His grip tightened with futility on his gun and cast a questioning glance at Red.

Red knew they were all walking on eggshells here. He had never seen the suave demon in such a state. It really brought home how out of his depth he really was when dealing with the supernatural.

Crowley drew a deep breath and twitched his shoulders back into something approximating relaxed. Voice once again calm, he continued. "Its still active. But whoever has it, is the one that owns you body and soul."

"That's-" Red swallowed the lump in his throat. "That's... disconcerting."

"In the meantime, the former Miss Rostova also know as the current Mrs. Agent Keen, is fair game to anyone and anything who might hold you responsible for losses incurred."

"I assure you, Mister Crowley, I had nothing to do with-"

"Yes, Raymond, you did." Crowley interrupted, voice cold. "You see, whoever this is, they took the time and the effort to single you out. You, Raymond. And if I find out this was in any way, shape, or form _your_ idea, I will take the girl and your guard dog," he gestured at Dembe. "Do I need to finish that threat? Or will your imagination suffice for what I will do to them?"

"Mister Crowley, there is no need. I will look into things on my end and I will let you know what I find," Reddington assured the demon.

"Do that. I'll be in touch. Toodles, Darling." Crowley moved to walk out the doorway, then paused. "Oh, before I go, do you have a business card for Yanof? I haven't found that perfect tailor yet and he looks like he knows his business."

"Do you promise not to kill him if it doesn't work out?" Red returned easily, slipping back into congenial concierge. "Please don't make me find a new tailor as well."

"Very well, but only because you asked nicely." Crowley plucked the card from Red's outstretched fingers then vanished into thin air.

"Brother, tell me you had nothing to do with..." Dembe gestured at the empty space where Crowley previously stood and the theft he represented.

"No." Red answered plainly. "No, nothing at all. It would seem I need to find out who's strings I will be dancing to."


	9. Answers

_.o0o._

" _Mrs. Keen? This is Dean Winchester. Hey... Uh, could we meet face to face? You asked me how much you should trust Red? Well, we had a few ideas about that. Call me when you get a chance."_

.o0o.

Elizabeth fidgeted in her chair, but it wasn't the chair's fault. The restaurant was a nice one, the furniture was comfortable, the food delicious. It had the prefect blend of privacy and visibility. Privacy, because she didn't was eavesdroppers. Visibility, because if this discussion didn't go the way she wanted it to then she needed her backup to see it. No, she didn't fidget because of the chair. She fidgeted because of nerves.

Thankfully, when Raymond Reddington agrees to a meet he was always punctual. Almost at the stroke of the hour, the older man strolled through the door. The maitre d' immediately recognized him (naturally, Liz sighed) and nearly tripped over his own feet escorting him to the table. With a small gracious smile, he sent the restaurant employee on his way.

"Lizzy," he greeted, taking his seat.

Despite her nerves, she couldn't help but notice that Red seemed... tired, and tense. He'd lost a few pounds in the last month and his pallor showed hints of gray. "Red? Are you alright?"

The older man offered her a weary smile. "Bad week at the office," he admitted. "Nothing that you need to worry about. I'll get it straightened out one way or the other sooner or later.

For a moment, Elizabeth felt a pang of guilt for confronting him like this, when he was already worn out and burdened, but she ruthlessly shoved the emotion down. Practically, she recognized that squaring off with an opponent that was already draggy could only work to her advantage.

As soon as the thought crossed her mind, Red made the visible effort to force his posture upright and sharpened his gaze on his dinner companion. Any reservations she had, melted away in that moment. Elizabeth should have known that the man wouldn't have shown up to her little tete-a-tete if he didn't think himself capable of handling the exchange.

"So my dear, what can I do for you today?"

Elizabeth took a deep breath before fixing a hard look and her face and setting her shoulders. "I want answers, whole answers. Not half truths and evasions. Answers."

Red leaned back and considered the young woman over his wineglass. Something had changed; he didn't know what yet, couldn't put his finger on it, but something had shifted. Still, he vented a soft chuckle. "Truth, like beauty, is in the eye of the beholder."

"Stop, Red. Just stop," Elizabeth snapped, heat in her voice. "We are not doing this dance. Tonight, you **are** telling me everything."

Bemused, Red asked, "And why would I do that?"

Wordlessly, Elizabeth Keen set a rolled up parchment on the table between them.

All air left Red's lungs. "Wh-? How?" The juxtaposition of a demon contract and his Lizzy temporarily stuttered his thought processes. He forced a deep breath to restore his equilibrium. "Do you know what that is?"

"I know its important to you. Very important."

"Do you have any idea what the owner of that contract is threatening? What he would do to _both_ of us?" Red demanded, aghast. He knew _Lizzy_ was not the original thief. But that wouldn't stop Crowley from doing his worse. And Red's imagination could conjure some terrifying demonic doings.

Elizabeth hesitated. She didn't know.

"And what, pray tell, would you do if I simply took that away from you? Right here, right now?" Red demanded further. "That roll of paper is more than worth creating a loud, bloody scene over."

Her face hardened. "I wouldn't let you."

"Between Dembe and myself, I am sure we could overpower you, Lizzy." Red chided.

Before she could retort, two large men plopped themselves down at their table on either side. The stockier of the two reached across Red and swiped the dinner bread from the basket. "Ah, I wouldn't expect too much help from Dembe, Mr. Concierge. He's taking a little nap in a locked closet right now," Dean Winchester informed him while chewing. "And honestly? Keen over there has a nasty right hook. I bet she'd give you two a run for your money."

"Winchesters." Raymond Reddington sighed heavily. "Of course the Winchesters. Always the Winchesters. What have you done?"

Sam smiled. It was not a reassuring smile. It was a smile full of malice and predatory glee. Red did not like he look of that smile. "Razed a little Hell."

"Razed-!?" Red swallowed back the words. "Do you have any idea what Crowley will do to all of us? Including Lizzy? She was never supposed to be part of this!" He hissed, fury building.

"Yeah, we saw when we read your contract," Sam agreed. "Later tonight, you're going to tell her **why**. Because, yeah, we know how pissed Crowley is. And if you don't answer all her questions, completely, when Crowley traces it back to us, we'll say you put us up to it."

"See, we got a garage full of car parts and a safe full of money saying you been smoozing us," Dean explained while drinking Red's wine.

"Then there's the security footage at the FBI Counter Terrorism Unit saying you came to us," Sam added. "Well, to Dean. I'm willing to bet Crowley can get a hold of those tapes. I mean, he got access to an NSA satellite for us before."

"Then we are all dead," Red growled. "How is dying en mass a plan?"

"Once upon a time, we kept Crowley chained up in our basement for months," Dean dismissed. "We can handle Crowley. But..." He trailed off, invitingly.

Grudgingly, Red prompted, "But?"

Smiling happily, Dean continued. "But, if you play ball with our girl here, your contract along with a few other big players' is gonna show up in the clubhouse of some Lucy Loyalists. They've been pulling together lately trying to put Lucy back in charge. Crowley will buy that they want to undermine him like that. They had access to the records a lot easier than us."

"Means, motive, and opportunity." Sam summed up, very lawyer-like. "Me and Dean are off the hook, Crowley has no reason to look at Lizzy, and no one looks twice at you. You are just a pawn in a power play."

"You poor little victim, you," Dean soothed mockingly. "And poor Crowley, spinning his wheels taking out some poor little black-eyed bastards who didn't do anything and don't know to go to ground."

"Everybody's happy," Sam finished.

"Except me," Red pointed out heatedly.

Dean shrugged. "I can live with that."

Red fell silent as he processed. After a bit, a tiny laugh escaped him.

"Something funny?" Sam asked.

"Every step of the way, Dembe kept warning me that you two were dangerous. Kept asking me if I was sure I knew what I was doing. I told him of course I did. You two weren't the most dangerous men on the planet I'd ever dealt with. _I_ wouldn't underestimate you." Red huffed another laugh. "I forgot how utterly insane and unpredictable you two can be."

Dean smirked. "Crazy works."

After a beat, Elizabeth broke the tableau by reaching into her purse. From it she drew a notebook. The three men men could see a list of questions: things Elizabeth wanted to know. She also uncapped her pen. "So," she said, looking Red hard in the eye. "I have questions. You will give me answers."


	10. Obligations Waived

Someone knocked at the door. For anyone else, that wouldn't be a problem. People knock on other people's doors all the time. Except, this was Raymond Reddington's door. No one, not the FBI, not Elizabeth Keen, not even Dembe knew which door the elusive man actually lived behind. It was safer that way. For everyone, but most especially for Red.

Gun in hand, the informant made his way to the security monitor to see who had found him. "Unexpected," Red whispered to the screen. Dean Winchester, looking more... ragged than usual. Well, that might explain why the infernal man would bother tracking him down. When Dean Winchester was looking ragged, then the world was probably about to implode. Again.

A heavy fist pounded on the door again. "Come on, Red. Don't be like that!" His voice sounded remarkably playful, in stark contrast to the lined face. Maybe the world wasn't about to end. Most likely he just got done saving it. "I can see the hidden camera, I know you know I'm here."

Intrigued, annoyed, and more than a little concerned, Red opened his door gun first. "Is there a particular reason why I should refrain from shooting you in the face, here and now?"

Dean had the gall to look affronted. "Seems a little harsh, don't ya think? All we did was make you tell the truth."

"You ruined year, _years_ , of planning!" Red exclaimed. "And you didn't even get anything out of it!"

"Hey, I torched _thousands_ of Deals and blamed it on the completely innocent demons," Dean paused to consider what he just said. "Except that, you know, they were evil demonic sons of bitches. You know what? Never mind. The point is I got away with screwing with Hell. You're just upset that the infamous Raymond Reddington was a side job and not the main feature."

With a heavy sigh, the gun lowered. Red gestured the younger man inside. What ever reason brought him here probably shouldn't be discussed in the open doorway. "What do you want? And how did you find me? I paid a witch good money to ward my home from every evil she could think of."

Dean snorted. "Yeah, cuz witches who get their mojo juice from demons are so trustworthy and would never bilk you. Or sell your address to Crowley."

"Crowley. Of course." Red poured two glasses of Johnny Walker Green and offered one to his unexpected caller. "Does he have another job for me and can't come himself? Or did he farm out my services to you and your brother?" Red could only imagine the headaches that would come with being at the disposal of the Hunters Winchester. His rampant imaginations stopped cold at Dean's next words.

"He's dead."

"I'm sorry, I believe I need to hear that again."

Three fingers of Johnny Walker vanished. "Crowley's dead."

"Honestly and truly?" Red demanded. "He didn't fake it, you're sure? Like he did last time when he was working with your angel, Castiel?"

"Yeah, we're sure. The bastard died stopping Lucifer, right in front of us. Took one for the team." Dean stared down into his glass, clearing seeing the event in his mind's eye again. "Did not see that coming."

"I'm not sure if condolences for your loss are appropriate or not. If I recall, your relationship was complicated at best." Red refilled the younger man's tumbler. "You came all the way out here to tell me the news? That seems... suspicious."

"Crowley... he, ah..." Dean sighed and drained his glass again. "Crowley left some stuff behind, in case something happened to him. He asked me to give you this."

Red accepted the box and nearly dropped it when he opened the latch. "Is this my contract? For my Deal?"

Dean nodded. "Yeah. Looks like the sonnova bitch went soft. See that?" He pointed to the last line of text, written in a rusty brown medium that was probably blood. "It reads, 'further obligations waved.' Do you know what that means?"

Red's mouth fell open in shock and he hardly dared to breath. "My soul..."

Dean nodded. "Out of hock. You are now officially your own man."

"Crowley cut me loose." Red almost couldn't believe it. In fact, he didn't believe it. The King of Hell would never do something altruistic. "Why?" he demanded sharply.

Dean shrugged. "Dunno for sure. Best I can figure, he listened when I put a bug in his ear that nobody wants to see you turned demon. Now, when your time comes, you go up or down and you stay there. If I were you, I'd start cleaning up my act. The basement is bitch."


End file.
